to start, I would buy the 30-30 setup; 9mm is minimal cost savings. For nice tuned loads, Atlanta arms and ammo supplies the ammo for a lot of competition shooters, you can get major and minor loads.
As mentioned, you will not save any money as you will shoot more. The benefit is in tuning the loads to your liking and being able to shoot more for the same cost. Plus it is fun to do with your kids, as a stress reliever, just to get away from work for a while and focus on something else. And if you are going shooting in the morning and you realized you forgot to buy ammo, head over to the bench and crank out a couple of hundred and you are good to go!
IMO, the cost savings only comes when you buy in bulk. If you aren't ordering 5k of bullets, 10k of primers, 8lb jugs of powder, etc., at a time, you really don't get a discount on the component cost, plus the hazmat fee will kill any savings unless you are ordering a lot at the same time. Small quantities are expensive.
Don't forget all the ancillary stuff you must have to load: scale, case gauge, adjustment wrenches, micrometer, etc. Not just as simple as getting a press and a set of dies.
Don't know where you are located, but I'm sure someone is close by and would have you come over and show you the ropes on a press. All the books in the world are great, but there is nothing like watching and learning from someone who has been there and done that. It will also let you try out a couple of different presses to see what you like and are comfortable with.
HTH,
Shannon